One of the Museum’s crown jewels is its drawing collection, numbering over 8,000 sheets. Collected since 1816, this distinctive trove is the country’s earliest public drawing collection. It is also one of the finest, whose strength resides in its unparalleled late 18th- and early 19th-century material to furnish a comprehensive survey of American art from its inception, dominated by European artists, up through the 1860s, by which time native-born artists had asserted an American identity. Stellar clusters after that time include around 640 drawings by James Carroll Beckwith, ten of which are the earliest portraits of John Singer Sargent known; six sheets by Sargent and watercolors by Louis Comfort Tiffany. Beginning with rare colonial objects collected for their historical interest, the collection documents major events in the history of the nation. It also records the cultural firmament, including the highly significant 217 16th-century watercolors of European birds by Pierre Eskrich and colleagues collected by their donor that antedate the publication of the first printed ornithological treatises.

While panoramic in scope, the New-York Historical Society's drawing collection encompasses large holdings by a single artist or group. Among the highlights are the 500 watercolors by John James Audubon, including all 435 preparatory for The Birds of America. These national treasures form the centerpiece of the Historical Society's Audubon holdings, the largest repository of Auduboniana in the world. Others are the 221 "outline" drawings of George Catlin recording Native American culture; an incredibly rich cluster of drawings by Hudson River School artists such as Thomas Cole, Jasper Cropsey, and John Frederick Kensett; and all the known watercolors by William Guy Wall for the seminal The Hudson River Portfolio (1820–1825), the namesake of the nation's first indigenous landscape school that set the itinerary for the American Grand Tour. It also numbers over 350 drawings and sketchbooks of Asher B. Durand.

Landscape, including cityscapes, is another significant category. The earliest is a 1650 view of New Amsterdam, after which a legion of draftsmen recorded New World topography. Following on their heels are followed by a cache of 194 works by William Rickarby Miller; 27 watercolors by George Harvey, 18 for his "Atmospheric Landscapes"; and 75 stunning works on paper by Thomas H. Hotchkiss. In addition, there are fascinating rare sketchbooks; a dozen panoramas, most spectacularly an eight-part one of Manhattan in 1842; 123 sheets by Baroness Hyde de Neuville; and watercolors by Nicolino Calyo, notably his large gouaches of the Great Fire of 1835 and his "Cries" of New York street vendors. Social realism in scenes by Robert Henri and Raphael Soyer, coupled with views by Oscar Bluemner, Richard Haas, Frederick Brosen, Eve Ashheim, and Béatrice Coron, bring this category into recent times.

Portraits, some portraying historical figures like Thomas Jefferson comprise another copious category. Noteworthy are pastels by James Sharples and Francis Cotes, John Vanderlyn's likeness of Robert Fulton, Native American portraits by Saint-Mémin and Albert Bierstadt, likenesses by folk artists, 88 watercolors by Enit Kaufman (a Who's Who), and many self-portraits of artists. Among the over 359 silhouettes, 24 are by the acknowledged master of the medium Auguste Edouart.

Around 4,000 works by illustrators feature landscapes and portraits or illustrate literary or journalistic works, as in the cases of Felix Octavius Darley, Charles Dana Gibson, William Glackens, and Chesley Bonestell. Exceptions include around 130 documentary Civil War sketches by eyewitness "sketch" artists before the widespread use of photography. So rich is the collection that it defies categorization. Unusual sheets range from watercolors by David Cusick, one of the first Native American artists, to frakturs, to works by graffiti artists, among them Tracy 168 known for his “Wild Style.”